Synthesis of the tetrasaccharide α-D-Glcp-(1→3)-α-D-Manp-(1→2)-α-D-Manp-(1→2)-α-D-Manp recognised by Calreticulin/Calnexin
2005 (English)In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 340, no 16, 2558-2562 p.Article in journal (Refereed) Published
The title compound as its methyl glycoside was efficiently synthesized using a block synthesis approach. Halide-assisted glycosidations between 6-O-acetyl-2,3,4-tri-O-benzyl-α-d-glucopyranosyl iodide and ethyl 2-O-acetyl-4,6-di-O-benzyl-1-thio-α-d-mannopyranoside using triphenylphosphine oxide as promoter yielded, with complete α-selectivity, a disaccharide building block in high yield. The perbenzylated derivative of this proved to be an excellent donor affording 88% of the protected target tetrasaccharide in an NIS/AgOTf-promoted coupling to a known methyl dimannoside acceptor. Deprotection through catalytic hydrogenolysis then gave the target compound in 47% overall yield.
Place, publisher, year, edition, pages
Elsevier Ltd , 2005. Vol. 340, no 16, 2558-2562 p.
Calreticulin substrates; Iodide glycosyl donors; Triphenylphosphine oxide promotion; Thioglycoside block donor
IdentifiersURN: urn:nbn:se:su:diva-23721DOI: 10.1016/j.carres.2005.09.001OAI: oai:DiVA.org:su-23721DiVA: diva2:194157
Part of urn:nbn:se:su:diva-4592005-04-182005-04-182010-10-21Bibliographically approved